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The Weeping Willow was originally a human woman targeted by the Slender Man. After extensive stalking and psychological torment which left this woman in a severe state of depression and anxiety, she was taken. Over the course of several months, she was further physically and mentally tortured until she was willing to take any way out of her situation, and The Slender Man was more than happy to oblige. However, a problem occurred, as she became angrily defiant of her captor, instead of obedient. She rebelled against her captor out of hatred for what it had done to her, which in turn, created a weaker mirror image of itself in her. As the first Afflicted to rebel in this manner and survive, she inadvertently inspired many other Afflicted to escape servitude.

The Weeping Willow and the Slender Man have been enemies ever since, with the similarity of chosen homes and victims leading to frequent clashes between the two.

The Weeping Willow most often appears as a young woman, with long brown or black hair and black (sometimes thorny) branches for arms. She can have anywhere from four to eight barren black branches extending from her back. The branches are flexible, sharp enough to leave gashes in stone, and unable to be retracted. She lacks eyes and a mouth, instead having black, empty voids where these would appear. Black ichor, which in fact is a replacement for blood, constantly leaks from the eye voids, leading her to appear as if she is constantly crying.

She commonly wears a plain, torn black or grey dress. Alternatively, she has been seen wearing a grey (or black) long-sleeved shirt and black jeans.

The sound of many voices sobbing in unison follows her and the sound of it varies depending on the listener - some have heard more than one pitch to the voices, some have heard children or infants crying, and some have heard the cries of animals.

Willow tends to live in well-shaded deciduous forests near suburbs and schools. She does not trust human beings and will attack those who wander into her forest. It has been observed that she will eat the corpses of her victims, as well as the victims of other Afflicted. She primarily preys upon the betrayed or hurt, particularly those who have suffered from depression at some point in time, by stalking and then kidnapping them.

Those stalked first experience increasing depression and paranoia, then hallucinations accompanied by delusional thoughts, and eventually some engage in self-harm, or attempt to take their own lives. Those that do not commit suicide usually disappear. If their body is found, they are usually in a state of severe mutilation, as if slashed apart or impaled several times. In all cases, death of the victim is determined to be the result of severe blood loss (despite this not actually being something a pathologist can put down on the death certificate).

Violent though she can be, she seems to take a certain protective interest in children and will usually spare them.

She has also appeared to "pity" certain targets, who instead become Melancholies (collectively, the Melancholy), Servants of hers somewhat similar to the Slender Man's Proxies. The method in which these Servants are created is always the same - the victim is forced to drink the Willow's Tears. It is unknown what is in the Tears that causes such a conversion to Willow's side, but it is known that breaking free from Servitude is incredibly difficult and can even be physically painful for a Melancholy. It is currently unknown why she even wants, or needs, Servants. It has been theorized that it is either for protection or a need for companionship.

The Weeping Willow was inspired by a major plot point in the ARG Corvidaek, where a young woman named Willow "Lenore" Ashens (played by DarkShadows) allowed the Slender Man to alter her into a more powerful creature in an attempt to prevent an alliance of Fears from destroying the human race.